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WO2008147022A1 - Composition antirides pour application externe sur la peau, contenant des dérivés de biflavonoïdes - Google Patents

Composition antirides pour application externe sur la peau, contenant des dérivés de biflavonoïdes Download PDF

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Publication number
WO2008147022A1
WO2008147022A1 PCT/KR2008/001038 KR2008001038W WO2008147022A1 WO 2008147022 A1 WO2008147022 A1 WO 2008147022A1 KR 2008001038 W KR2008001038 W KR 2008001038W WO 2008147022 A1 WO2008147022 A1 WO 2008147022A1
Authority
WO
WIPO (PCT)
Prior art keywords
cosmetic composition
biflavonoid
derivatives
improving skin
skin wrinkles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2008/001038
Other languages
English (en)
Inventor
Chanwoo Lee
Eunrhan Woo
Hansung Kim
Song Yi Lee
Hyunjung Choi
Ji Yeong Kim
Jinwong Kim
Duckhee Kim
Han Kon Kim
Ihseop Chang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Amorepacific Corp
Chosun University Industry Academic Cooperation Foundation
Original Assignee
Amorepacific Corp
Chosun University Industry Academic Cooperation Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Amorepacific Corp, Chosun University Industry Academic Cooperation Foundation filed Critical Amorepacific Corp
Priority to CN200880018472A priority Critical patent/CN101730520A/zh
Publication of WO2008147022A1 publication Critical patent/WO2008147022A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9739—Bryophyta [mosses]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9741—Pteridophyta [ferns]
    • A61K8/9749—Filicopsida or Pteridopsida
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9771—Ginkgophyta, e.g. Ginkgoaceae [Ginkgo family]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • the present invention relates to a cosmetic composition containing biflavonoid derivatives as an active ingredient for improving skin wrinkles caused by aging.
  • the present invention relates to an anti-wrinkle cosmetic composition containing biflavonoid derivatives as an active ingredient, which is safe for the application on the skin without side-effects, induces procollagen production, inhibits MMP-I, and has the effect of improving wrinkles generated by UV.
  • Skin aging is largely divided into two groups according to the reason; one is intrinsic aging caused by the aging of the structureand physiological functions of the skin and the other is extrinsic aging caused by accumulated stress given from outside such as sunrays, etc.
  • UV among the sunrays is well-known as a reason of aging.
  • the horny layer of the skin becomes thicker and the major structural constituents of the skin, collagen and elastin, are denatured, resulting in wrinkles by lack of elasticity.
  • Skin aging accompanies various functional, structural changes.
  • the skin composing components, epidermis, dermis and subcutaneous tissue become thinner.
  • ECM extracellular matrix
  • ECM is composed of two main components. One is elastic fiber taking 2-4% of ECM and the other is collagen taking 70-80% of ECM. According to aging, the skin greatly loses its elasticity, which is resulted from the decrease of collagen and elastin.
  • the collagen and elastin are regulated by various factors.
  • collagen and elastin are decomposed by the expression of matrix metallo protease such as collagenase and elastase, so that the collagen content in skin is reduced.
  • matrix metallo protease such as collagenase and elastase
  • retinol and retinoic acid The most effective method to prevent skin aging so far is to use retinol and retinoic acid.
  • the improvement effect of retinol and retinoic acid on wrinkles and elasticity has been well-informed through previous reports (Dermatology therapy, 1998, 16, 357 ⁇ 364) .
  • the retinoid has positive effects such as wrinkle or elasticity improvement, it has problems of irritating skin even with only a small amount and being so unstable that it is easily oxidized and denatured when being exposed on the air, -and it causes the limitation to use. Therefore, studies have been going on to make the retinoid more stable, but skin irriation, the stability problems, remains unsolved.
  • the present inventors studied to find out a novel anti- aging material that is safe in human skin and has excellent anti-wrinkle effect among natural plant materials.
  • the natural plant originated biflavonoid derivatives not only inhibited the activity of collagenase but also exhibited improvement effect on wrinkles caused by UV and at the same time excellent safety on human skin.
  • the present inventors further observed that the biflavonoid derivatives had excellent preventive and therapeutic effect on skin aging. So, the present inventors completed this invention by confirming that a cosmetic composition for improving skin wrinkles of the invention which contained biflavonoid derivatives by 0.001-10 weight% more preferably 0.01-5 weight! for the total weight of the composition had excellent wrinkle improvement effect.
  • the present invention is completed by the following steps: preparing an extract containing biflavonoid derivatives from natural plants by using water or an organic solvent; separating the biflavonoid derivatives by separation/purification process; measuring procollagen productivity and inhibition of collagenase decomposition; and confirming suppressing effect of the biflavonoid derivatives on wrinkles caused by UV.
  • the biflavonoid derivatives can be extracted from medicinal herbs or plants such as Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica, Lonicera japonica, etc, but not always limited thereto.
  • the biflavonoid derivatives can be included by 0.001-10 weight% for the total weight of the cosmetic composition for prevention and improvement of wrinkles and more preferably included by 0.01-5 weight%.
  • biflavonoid which is the active ingredient of the composition for prevention and improvement of wrinkles is described in detail.
  • the b ' iflavonoid derivatives, the active ingredient of the cosmetic composition for improving wrinkles, are the compounds represented by the following formulas 1 - 7.
  • the biflavonoid derivatives represented by formulas 1 - 7 can be obtained from natural medicinal herbs or plants such as Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica, by the conventional extraction and separation method.
  • To extract a target material stems, roots and leaves were dehydrated properly, followed by macerated or dehydrated only.
  • the target material was purified by the conventional purification method known to those in the art.
  • the synthetic compound or its derivatives corresponding to the above plant originated biflavonoid derivatives represented by formulas 1 - 7 .can be purchased on the market or can be synthesized by the conventional method well-known to those in the art. Specifically, the compound can be extracted from medicinal herbs or plants such as Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica, or synthesized by the conventional chemical synthesis.
  • panduratin derivatives represented by formulas 1 - 7 can be separated and purified from the extract extracted from Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica by using an organic solvent or from oil obtained from the above by compressing.
  • Biflavonoid derivatives can be extracted from such plants as Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica, but not always limited thereto.
  • Biflavonoid is a compound that is naturally generated in vascular plants and has the morphology of dimer formed by C-C or C-O-C bond. It is believed that the reason why the biflavonoid is in dimer form in plants is that when a stimulus is coming in from outside, a plant activates its in vivo protection system to protect itself, in which single molecular polyphenol structure is developed into biflavonoid.
  • the structure of biflavonoid is divided largely into two groups according to the bond types; one is amentoflavone having C-C bond and the other is ochnaflavone having C-O-C bond.
  • the biflavonoid derivatives of the present invention can be separated and purified from the organic solvent extract or oil prepared from medicinal herbs or plants such as Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica.
  • the extraction solvent can be water, methanol, ethanol, propanol, isopropanol, butanol, acetone, ether, benzene, chloroform, ethyl acetate, methylene chloride, hexane, cyclohexane, petroleum ether or a mixture thereof.
  • the separation and purification of biflavonoid derivatives from the natural plant extract can be performed by column chromatography filled with synthetic resins such as silica gel or active alumina and High performance liquid chromatography (HPLC) respectively or together.
  • synthetic resins such as silica gel or active alumina and High performance liquid chromatography (HPLC) respectively or together.
  • HPLC High performance liquid chromatography
  • the methods for extraction, separation and purification of the active ingredient are not always limited thereto.
  • the preferable content of the biflavonoid derivatives of the present invention in a cosmetic composition for improving wrinkles is 0.001-10 weight% for the total weight of the composition. If the content is less than 0.001 weight%, anti- wrinkle effect will not be obtained. In the meantime, if the content is more than 10 weight%, safety or formulation will matter.
  • the biflavonoid derivatives are preferably contained by 0.01-5 weight% for the total weight of the composition.
  • the content of the biflavonoid derivatives is not always limited thereto.
  • the cosmetic composition for improving wrinkles of the present invention can additionally include other anti-wrinkle elements that can raise the anti-wrinkle effect of the composition as long as they do not damage the original targeted anti-wrinkle effect.
  • the formulation forms of the cosmetic composition for improving wrinkles of the present invention are not limited, and can be nutritional toner, softener, nutritional cream, massage cream, pack, gel, astringent, essence, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water, powder, body lotion, body oil and body essence, etc.
  • the biflavonoid derivatives can be isolated from natural plants such as Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica, but herein Selaginella tamariscina was selected as an example.
  • Dried Selaginella tamariscina was pulverized and mixed with alcohol, followed by elution. Then, the solvent was eliminated and the crude extract was concentrated. The concentrated crude extract was mixed with ethyl acetate, and then ethyl acetate soluble component was extracted. Preferably, this extraction process was repeated at least three times. The extracted ethyl acetate soluble component contains biflavonoid derivatives, which already exhibited collagenase inhibitory activity despite it was not a single component. Then, ethyl acetate was eliminated to concentrate ethyl acetate soluble component. According to the difference of polarity, each component was separated.
  • a solvent was prepared by mixing chloroform, methanol and water at the ratio of 10 : 1 : 0.5 (v/v) .
  • the component was mixed with this solvent and 10 fractions were separated thereby.
  • the fractions proceeded to column chromatography to separate pure single anti-wrinkle component.
  • the anti-wrinkle component obtained from the above extraction and separation was proved to be amentoflavone having the structure of formula 1.
  • the methods for extracting biflavonoid derivatives, amentoflavone, 2' , 8"-biapigenin, taiwaniflavone, robustaflavone, ginkgetin and ochnaflavone, from Selaginella tamariscina, Ginkgo biloba, Cephalotaxus koreana, Nandina domestica and Lonicera japonica are similar to the above method.
  • Fig. 1 is a set of photographs illustrating the improvement of wrinkles caused by ultraviolet (UV) by biflavonoid derivatives.
  • Example 1 Extraction of sumaflavone 1.8 kg of dried Selaginella tamariscina was cut into small pieces, followed by extraction with methanol at 80 ° C for 4 hours, which was repeated three times. The obtained methanol extract was concentrated under the reduced pressure. 78.7 g of the concentrate was dissolved in water, to which methylene chloride was added as an extraction solvent, followed by extraction over three times. The methylene chloride soluble fraction (21.7g) was obtained and the remnants proceeded to extraction again using ethyl acetate or butanol as an extraction solvent over three times.
  • the ethyl acetate soluble fraction ( ⁇ .8g), the butanol soluble fraction (7.8g) and the remaining water fraction (16.2 g) were obtained.
  • ⁇ .8g of the ethyl acetate soluble fraction proceeded to silica gel column chromatography.
  • a mixed solvent comprising chloroform, methanol and water at the ratio of 10:1:0.1 (v/v) was used as a column elution buffer.
  • Column chromatography was performed with raising methanol content slowly to increase polarity of the mixed solvent, resulting in 6 fractions (El- E6) .
  • Amentoflavone, 2' , 8"-biapigenin, taiwaniflavone, robustaflavone, ginkgetin and ochnaflavone were also prepared by the same manner as described above.
  • Fibroblasts separated from human skin were inoculated in a 24-well plate by 10 6 cells/well, followed by culture until they grew 90%. Then, the cells were cultured in a serum-free medium for 24 hours. 4-substituted benzoic acid derivative compound having 3, 4-methylenedioxy or 3, 4-ethylenedioxybenzene moiety, obtained in Examples 1-2, was dissolved in the serum- free medium was treated thereto at the concentration of 10 ⁇ 4 , followed by culture in a CO 2 incubator for 24 hours. Supernatant was separated and procollagen level was measured using procollagen type 1 ELISA kit. The results are shown in Table 1 and the biosynthesis capacity was presented by the ratio to non-treated group (considered as 100%) . [Table 1]
  • Human fibroblasts were inoculated in a 96-well microtiter plate containing DMEM (Dulbecco's Modified Eagle's Media) supplemented with 2.5% FBS at the concentration of 5,000 cells/well, followed by culture till the cells grew 70-80%.
  • the sample compound was treated thereto at the concentration of 10 "4 for 24 hours and then the cell culture solution was collected.
  • Collagenase production in the cell culture solution was measured by using a commercial collagenase measuring kit (Catalog #: RPN 2610, Amersham Pharmacia, USA).
  • the collected cell culture solution was loaded in a 96-well plate evenly distributed with the first collagenase antibody, followed by antigen-antibody reaction in a thermostat for 3 hours.
  • the chromophore-conjugated second collagen antibody was added to the 96-well plate, followed by reaction for 15 minutes. 15 minutes later, coloring material was added thereto to induce color development for 15 minutes at room temperature and then the reaction was terminated by adding IM sulfuric acid.
  • the reaction solution was yellow. According to the degree of the reaction, the degree of yellow color varied, optical density ⁇ s (OD405) of the yellow 96-well plate was measured by using a spectrophotometer and collagenase production was calculated by mathematical formula 1. At this time, the OD of the cell culture solution not- treated with the sample compound was considered as control.
  • Collagenase Expression Level (%) (OD of the group treated with the sample compound/0D of control) XlOO
  • MMP-I matrix metallo protease
  • UV was irradiated to the mice from 70 cm distance three times a week for 10 weeks (total 30 times) to cause wrinkles.
  • the sample material and the positive control material were transdermally administered by 100 ⁇ L, twice a day (morning/afternoon) , 5 days a week (Monday - Friday) for
  • a cosmetic composition for improving wrinkles containing biflavonoid derivatives can be selected at random from the group consisting of nutritional cream, nutritional lotion, massage cream, nutritional essence, and softener, etc.
  • Nutritional toner (milk lotion)
  • Nutritional toner containing biflavonoid derivatives was prepared by the conventional method according to the composition shown in the below table.
  • Softener containing biflavonoid derivatives was prepared by the conventional method according to the composition shown in the below table.
  • Nutritional cream containing biflavonoid derivatives was prepared by the conventional method according to the composition shown in the below table.
  • Pack containing biflavonoid derivatives was prepared by the conventional method according to the composition shown in the below table.
  • Gel containing biflavonoid derivatives was prepared by the conventional method according to the composition shown in the below table.
  • the biflavonoid derivatives of the present invention interact with biflavonoid receptor to increase procollagen biosynthesis, so that they can have the effect of inhibiting wrinkle generation caused by lack of skin elasticity resulted from the denaturation of collagen, one of the important skin components, and of inhibiting the expression of collagenase, the enzyme decomposing collagen, and thereby increases improvement of wrinkles caused by UV. Therefore, the cosmetic composition containing the biflavonoid derivatives as an active ingredient of the present invention can be effectively used as a cosmetic composition or an agent for improvement and prevention of wrinkles without side effects .

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  • Engineering & Computer Science (AREA)
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  • Natural Medicines & Medicinal Plants (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition cosmétique destinée à améliorer les rides cutanées, qui contient des dérivés de biflavonoïdes en tant qu'ingrédients actifs. La composition cosmétique contenant lesdits dérivés biflavonoïdes de la présente invention peut être appliquée en toute sécurité sur la peau sans provoquer d'effets secondaires. En outre, elle permet également d'améliorer l'état des rides provoquées par les UV, par le biais de la production de procollagène et de l'inhibition de MMP-I.
PCT/KR2008/001038 2007-06-01 2008-02-22 Composition antirides pour application externe sur la peau, contenant des dérivés de biflavonoïdes Ceased WO2008147022A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN200880018472A CN101730520A (zh) 2007-06-01 2008-02-22 含有双类黄酮衍生物的皮肤外用抗皱组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2007-0053700 2007-06-01
KR1020070053700A KR100902173B1 (ko) 2007-06-01 2007-06-01 바이플라보노이드를 함유하는 피부 주름 개선 화장료

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WO2008147022A1 true WO2008147022A1 (fr) 2008-12-04

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KR (1) KR100902173B1 (fr)
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WO (1) WO2008147022A1 (fr)

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WO2010090001A1 (fr) * 2009-02-09 2010-08-12 株式会社資生堂 Agent de blanchiment de la peau, agent antivieillissement et agent antioxydant
US10251832B2 (en) 2017-05-26 2019-04-09 Mary Kay Inc. Cosmetic compositions and methods
CN115894424A (zh) * 2023-01-06 2023-04-04 中日友好医院(中日友好临床医学研究所) 新型双黄酮类化合物及其制备方法、药物组合物和应用

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KR101117561B1 (ko) * 2008-12-09 2012-02-29 주식회사 코리아나화장품 플라보노이드계 화합물을 유효성분으로 함유하는 항노화 화장료 조성물
KR20120009953A (ko) * 2010-07-23 2012-02-02 (주)아모레퍼시픽 아멘토플라본을 함유하는 자외선에 의한 피부 세포 손상 방지용 조성물
KR102046331B1 (ko) * 2013-10-10 2019-11-19 주식회사 엘지생활건강 마그놀롤 또는 히노키플라본을 포함하는 피부 볼륨증가 및 주름개선용 화장료 또는 약학 조성물
KR102196952B1 (ko) * 2018-12-27 2020-12-30 광주여자대학교 산학협력단 남천 잎 추출물을 유효성분으로 포함하는 피부재생 촉진용 조성물
KR102335262B1 (ko) * 2019-09-26 2021-12-07 한국생명공학연구원 셀라지넬라 로씨 추출물을 포함하는 피부 노화 방지 및 피부 주름 개선용 화장료 조성물
KR102316415B1 (ko) * 2019-11-22 2021-10-21 광주여자대학교 산학협력단 남천을 이용한 화장료 조성물의 제조방법
KR102316407B1 (ko) * 2019-11-22 2021-10-21 광주여자대학교 산학협력단 남천을 이용한 화장료 조성물
CN115778866B (zh) * 2022-12-29 2025-02-28 云南大学 三尖杉提取物在化妆品或制备药品中的应用

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CN115894424B (zh) * 2023-01-06 2023-05-12 中日友好医院(中日友好临床医学研究所) 新型双黄酮类化合物及其制备方法、药物组合物和应用

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CN101730520A (zh) 2010-06-09
KR20080105730A (ko) 2008-12-04

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